A Heart to Win
by TwiAddictAnne
Summary: He's a bad boy on a mission. She's the girl who's dating his brother. What will happen when their worlds collide? Will he be able to win her heart? Will he even want to? OOC. All Human. Non-canon couples. Rated MA for language and adult situations. Gold prize winner for the Overall Story in the Villains Turn Contest.


**A Heart to Win**

 **Disclaimer:** **The author does not own any publicly recognizable entities herein. No copyright infringement is intended.**

 **A/N: This was my entry piece for the Villans Turn Contest. It won the Gold prize for the Overall Story among others. A big shout out goes to my beta, Ashmerlin, for her help and support. Happy reading. :)**

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 **A Heart to Win**

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"Oh for fuck's sake! You aren't still hung up on that stuck up bitch, are you?" Damon Salvatore asks his business partner, Matt Donovan, as he walks into the conference room.

Matt looks up at him through bloodshot eyes "Don't call her that." He said in a voice rough with emotion.

Damon rolls his eyes at him. "You need to get laid, man. I've never laid eyes on that chick, but I'm sure she's not worth all this moping."

Matt throws him a disgusted look over his shoulder and snaps, "Easy for you to say. She's seeing _your_ brother after all."

For a moment, Damon is too astounded to speak and then he bursts into laughter. "Really? Your ex is screwing my baby brother now?"

His best friend scowls at him. "Laugh it up, asshole. You're not the one who lost his girlfriend to a _kid_ anyway."

"Please!" Damon responds with a snort. "I'm Damon Salvatore. I don't get hung up on girls. I fuck them and then move on. So there's nothing for me to lose anyway."

"Oh yeah?" Matt asks in an angry voice. "Elena's different. You can't help but fall in love with her."

"Pfft. I could."

Matt shakes his head. "You can't. That's simply not possible."

"You wanna bet on that, Donovan?"

His cockiness infuriates Matt even more, and without thinking, he holds out a hand for him to shake. "You're on, Salvatore."

"This's gonna be fun."

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Damon watches his brother carefully as he takes a bite of his steak, his mind already in planning mode. "So, Stef," he starts casually. "How's life?"

Stefan smiles as he finishes his mouthful before answering him. "Life's good, brother. It's great actually."

Stefan's smile tells Damon what he needed to know. His brother is happy and that pisses him the hell off.

Being only two years younger to him, Stefan always seemed to have been their parents' golden boy. The thought that he had a girl who seems to make him sickeningly happy makes Damon feel like throwing up.

Plastering a fake smile on his face, Damon gives his brother a silent nod of his head before observing, "You seem happy."

"I am happy," Stefan replies. "Very much so."

"Anything you want to share with this big brother of yours?"

Stefan rolls his eyes and grins. "You have barely two years over me, Damon. You're hardly my big brother." Something in Damon's face must have caught his attention though because he backtracks and adds, "You're more like my best friend than big brother."

Damon swallows back the angry retort that bubbles up in his throat, wanting to point out that growing up everything that went wrong was supposedly his fault _because_ he's the "big brother". Instead, he just raises a questioning eyebrow at Stefan.

Unable to hold it back anymore, Stefan spills the beans—just like Damon knew he would. "Ok. It's a girl. Her name's Elena Gilbert and ..."

"Whoa! Hold up," Damon interrupts, holding a hand up. "Elena Gilbert? Didn't she use to be Matt's girlfriend?"

Stefan seems barely fazed by the question as he brushes it off. "Well, yeah, but she's not anymore. She finally realized that Matt is too old for her and agreed to give me a chance instead."

A part of Damon wants to chastise his little brother for stealing another man's girlfriend, but a bigger part, the part that knows that his brother doesn't give two shits about what he thinks, shuts him up. Of course, he can't stop the cocky remark from passing his lips. "What's up with this chick? Does she have bourbon flavored nipples or something?"

His words have an immediate effect as Stefan stands up from their table abruptly, looking like he's about have an aneurism. "I'll not tolerate you saying disrespectful things about her," he says through gritted teeth.

Damon holds his hands up in surrender. "Just kidding, brother. Sit down." He waits until Stefan is sitting across from him again before asking, "So it's serious, huh?"

"As a heart attack," his brother says. "I love her, D."

"Well, bring her over to my place one day then. I need to meet this girl that has Stefan Salvatore wrapped around her little finger."

When Stefan nods after a long moment of silence, Damon smiles to himself. _This is gonna be like taking a candy from a baby._

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The sound of the doorbell ringing makes Damon drop the shirt he has been considering wearing and makes his way to the front door. Opening it, he frowns. "You're early," he says.

"And you're not dressed yet," his brother answers as he takes a step inside the house. "It's good to see you tidied the place up a little."

Damon closes the door and turns to his brother, preventing Stefan's perusal of his house. "You're also alone. Where's the lovely Elena?"

Stefan shrugs. "She'll be here soon. I thought I'd come ahead of her and help you out. I didn't think you'd be prepared to have guests."

"I'm wounded, brother," Damon says pretending to be hurt as he rubs his bare chest. "You think I'm that anti-social?"

The truth is, he _is_ that anti-social. He can't even remember the last time he had anyone over aside from a few one-night stands here and there.

Rolling his eyes, Stefan says, "I didn't want her to come and run into any of your conquests. Does that answer your question?"

"You must think I'm a heathen." Of course Stefan didn't know that for the past few weeks now, all Damon could think of was Elena Gilbert. He had joked about her having bourbon flavored nipples, but the thought of pouring bourbon on her and then sucking it off of her nipples had become a fantasy of his lately.

A timid knock on the door makes them stop, and when Damon opens the door, he finds himself caught in a spell. The woman standing in front of him has to be the most beautiful creature he has ever laid eyes on. From her deep soulful brown eyes to her perfectly cascading mahogany hair, she looks like the reincarnation of everything that's pure and beautiful.

Her eyes widen as they fall on his chest, and then as if snapping out of a spell she quickly brings her eyes to focus on his face. "I'm Elena," she starts uncertainly, reaching her hand out for him to shake.

"Damon Salvatore," he responds, taking her hand in his and bringing it to his lips.

With utmost pleasure, Damon notices blood rushing to her cheeks as she looks into his eyes.

Of course, Stefan being the bratty one, has to butt in and ruin the moment. "Babe, this is my brother," he says, stepping up beside Damon before turning to his brother. "Weren't you planning to get dressed, D?"

Damon sighs audibly at that. "You're such a prude!" he says. Before walking up to his room, he winks at Elena and her answering blush makes him grin.

 _This is going to be fun._

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The dinner leads to a lunch invitation in the following week which results in more plans to spend time together. Of course Stefan is always there sitting between them and boring him to tears with his take on philosophy in the medieval ages, but Damon trudges through it all. Stefan's just a necessary evil, he tells himself.

It takes him a whole month before he finds the perfect opportunity to make his move.

On a day in mid December, Damon calls his brother from his office. Stefan greets him warmly, courtesy of their recently mended brotherly bonds.

After chatting for a few minutes, Damon broaches the subject causally. "Hey, Stef? Do you have any plans for Christmas this year?"

"Christmas eve or the day of?"

"Christmas eve," Damon replies. "I was wondering if you wanted to come to the office party this year?"

Stefan sounds genuinely sad as he answers, "I can't. I have that interview in New York, remember? Besides, I think it'll be weird with me and Matt in the same room."

 _Of course, I remember_ , Damon thinks. _That's the reason I'm so interested in hosting the party this year._ To his brother, he says sadly, "Donovan's out of town, man. He's spending the holiday season with his family. So I guess I'll be left to attend it alone."

Just like he expected, Stefan softens at his tone. "How about you take Elena to the party then? Her parents passed away around this time last year. So she must be feeling lonely. What do you think?"

 _I think you're one stupid asshole._ Damon tries not to let this thoughts show in his voice as he agrees, seemingly begrudgingly.

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Damon feels his breath catch in his throat as his eyes take in the woman standing before him. "You look amazing," he says, unable to stop himself from voicing his thoughts.

A shy smile appears on Elena's face as she bows her head a little in silent thanks. "Shall we go?" she asks timidly.

He holds his hand out for her and when her hand is in his, he motions to the limousine behind him and says, "Your chariot awaits, Milady."

Once we're in the party, Damon keeps Elena tucked next to him as he makes rounds of the room, introducing her to the guests. Not once does he say who she is to him though. As he doesn't want to introduce her as his brother's girl and he can't very well introduce her as his.

As people start making their way to the dance floor, Damon watches her sip her drink as she looks around. She must have felt his gaze on her because she turns to face him and smiles. "This is a great party, Damon. Thank you for bringing me here. I would've hated to stay home alone tonight."

"You don't need to, Elena," he starts before catching himself. "Not when you have me as your friend."

"I'm a lucky girl indeed." Her smile broadens as she leans into him and whispers, "I think your secretary is planning my painful demise because of it though."

His eyes seek out his secretary, and sure enough, she's standing at the corner of the room, shooting daggers at them. "Rebecca can be a bit prissy, but she knows her job," he admits, regretting the one time he had allowed Rebecca Michelson to give him a head under his desk.

Something in his expression must have tipped Elena about that secret though because the next thing he knows, he's being led to the dance floor by a determined-looking Elena.

"Whoa! What's up?" he asks when she lets go of his wrist in the middle of the dance floor.

"I feel like dancing," she answers with a shrug.

A surprised chuckle escapes him as he holds out his hand to her. "May I have this dance, Ms. Gilbert?" he says formally, bowing his head over her hand as he does so.

She offers him a smile as she nods. "You may, Mr. Salvatore."

Damon takes her hand in his as he twirls her around once before bringing her closer to him, making their bodies move in a perfect waltz. She looks up at him after a heartbeat and their eyes lock on each others. To him, it feels like time has stopped because no matter how much he had bragged to his friend about being able to stay detached from her, he realizes that he can't, not anymore.

And then, the song ends only to transform into a more upbeat tempo. The people around them go from dancing the coy and sensual waltz to a mass of bodies grinding against each other. Elena's hand slips from Damon's shoulder as she starts to move away, but he grasps her wrist and reels her into his embrace once more.

Her eyes seek out his, looking for answers to some unasked questions. Holding her gaze, he slips his hands up to take her arms and loop them around his neck. She doesn't fight him as he tightens her hold on him and starts to move to the music.

One moment Damon feels like he's doing the seducing while in the next, he finds himself being mesmerized by the amazingly beautiful woman in his arms. He waits for a moment before slowly letting his hands drop to encircle her waist. She stops breathing, he feels the shiver run through her body. That's all the incentive he needs to lean down and bring his lips impossibly closer to hers.

Her eyes widen infinitesimally at his sudden close proximity. "What are you doing?" she asks, her voice shaking a little.

He doesn't close the gap between them. Instead, he leans his forehead down on hers and sighs. "Setting an example of self-control," he whispers. "I should get you home."

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The car ride back to her place is uncomfortable. So many words left unsaid hang between them as they both try to act nonchalant on their sides of the limo. When the car pulls into her driveway, Damon exits the car to open her door for her. She gives him a brief look and steps out.

As he starts to walk beside her toward her door, she looks at him. "What are you doing, Damon?"

"Walking you home," he answers like it's the most natural thing to do.

She doesn't say a word as they walk the rest of the way. When they reach her door, he calls her name softly, "Elena …"

A choked sound of frustration comes out of her in response, and then she turns and pulls his lips down to hers. One moment. For one single moment, Damon contemplates taking her up on the offer … to win the bet. And then he realizes that it's not about the bet anymore. He doesn't even truly care about the stupid bet. No, he cares about her.

The thought makes him pull away from the kiss that had begun to ensnare his senses. He holds her at arm's length and repeats her question from earlier in a hoarse voice, "What are you doing, Elena?"

She opens her eyes slowly and bites her lip, suddenly looking uncertain of herself. "I was … uh …" Her cheeks redden as she stops to take a breath, and then she says, "I have lost the battle, Damon. I don't have the self-control to stay away from you anymore."

Her words do fill him with something that he hasn't felt in a long time—happiness. He holds her eyes captive in his as he shouts out to his driver, "Tyler, go home and have some time with your family."

Tyler leans his head out of the window to take a look at his boss's smiling face, salutes him and then promptly drives away, leaving the couple standing in the driveway.

Damon waits until they're alone before carefully taking Elena's face between his hands and asks, "Are you sure?"

She nods. "I'm sure about you."

Four words. Four simple words from her makes his control slip as he wraps her up in his arms and crashes his lips on hers. She kisses him back just as forcefully, wrapping her legs around his hips. With a groan, he separates himself from her long enough to motion her to open the door.

Once they are inside her house, Damon closes the door and pushes Elena against it, holding her captive between the unyielding door and his body. He presses his lips to her again and again until he feels the need to breathe and lets his lips trail down her throat.

When he finds his path obstructed by the ribbons holding her halter top in place, he moves his hand behind her neck and slowly undoes the tie. Her dress gives way, revealing her perfectly toned body to him. He traces the tops of her breasts with his lips when she lets out a whimper, her hands clawing at his back in an attempt to bring him closer.

The sound of her whimper lifts the haze he's been in, and he moves away to take her hand in his. She looks up at him and rises on her tiptoes to kiss the corner of his mouth before leading him toward her room.

Stepping inside her room, her scent assaults him from every direction, making him forget any and everything but her, the lust returns in full force. Damon pulls the dress the rest of the way off. Standing back he admires her body before ridding her of the scraps of lace covering her before taking her in his arms and placing her on the bed.

He takes a step back to peruse her naked beauty and feels his breath leave him at the sight of her. When she holds a hand out to him, he can't deny himself anymore. He shrugs off his jacket, his shirt and lets his pants join her dress on the floor before climbing up her body to lay a kiss on each of her eyelids.

A soft smile takes over her face as she encircles him in her arms and kisses him back with every bit of the passion he feels coursing through his body.

He takes his time worshipping her body, kissing her, teasing her, making her feel cherished with each stroke of his finger and each pass of his tongue. He revels at the sight of her flushed body as she twist and turns in his arms, seeking friction and letting out frustrated whimpers when he simply moves his lips to kiss some other place on her body.

"Damon, so help me God if you don't …" she starts, looking like a fiery Goddess as she lies beneath him.

The sight makes him smirk because as much as he enjoyed the shy purity of her character, he fucking loved this angry kitten side of her. Without any preamble, he rubs himself against her entrance once more like he has been doing for the past few minutes before slipping inside of her warmth for the first time.

A satisfied groan escapes him as he feels her stretch to accommodate him and her wet warmth welcoming him. He looks at her and sees her eyes snap shut as she throws her head back in ecstasy. He smiles widely and then, he starts to move.

They move in perfect countermotion, pushing each other higher and higher until they're both there … ready to jump off the cliff. He trails his hand down her body to find where they're joined and leans his head down, taking one of her nipples into his mouth, sucking hard. That's all it takes to send her flying off the cliff, her release bringing him with her.

Utterly spent, Damon falls asleep in the arms of the woman he knows that he's slowly but surely falling in love with.

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The bliss from the night before doesn't disappear when he wakes up the next morning. In fact the small feeling of tenderness in his heart morphs into pure adoration when he walks into Elena's kitchen to find her making pancakes for him … with nothing but his shirt covering her body.

Lazy morning kisses turns into all-consuming love-making right in the middle of her kitchen and then he finds himself sitting cross-legged on the floor across from her as she shares bits and pieces of her life with him. He feels rage course through him when she tells him how she had a twin sister whom her parents gave up for adoption because they were both college students at that time and unable to take care of two babies.

He feels his heart ache for her as she recounts her feelings of devastation when her parents passed away. She had sought out her twin after going through a great deal of trouble only to find out that her sister was terminally ill with cancer.

When he sees teardrops crawl down her cheeks as she remembers watching her sister fade away before her very eyes and not being able to do anything, he pulls her into his arms and holds her tight as she mourns her sister with him.

That night, Damon doesn't want to possess her like he has in the past month. Instead, he spends the night showing her that she isn't alone … not anymore … not when he's with her.

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Two days later, Damon stands in his house, his arms wrapped around Elena's waist from behind as they both look out the window, waiting for the inevitable other shoe to drop—Stefan's homecoming.

The sound of wheels on the gravel makes her back stiffen. Sensing her obvious distress, Damon pulls her hair to the side and kisses her neck. "You don't have to face him, you know? I can handle it."

"No," she replies, her face a mask of determination in spite of her shaky voice. "This is something we both want. So we'll face him together."

Damon takes her chin between his thumb and forefinger, tilting her head to the side to find her eyes. "Baby, are you sure? This isn't going to be pretty."

She swallows thickly and nods. "Yes, I want _you_ , Damon. You make me feel alive like no one's even done before. I …"

She doesn't get to finish her sentence as the doorbell rings, indicating that his brother is back. Holding her hand in his, Damon moves to open the door. "Hello, brother," he greets.

"Hey, D …" Stefan stops midway as his eyes fall on Elena before quickly following her hand holding Damon's. "Elena, why are you here?"

Elena takes a deep breath and says, "Because I want to be."

He looks taken aback by her words. "Oh! I didn't know you two had become such great _friends_." It doesn't escape Damon's notice when his brother emphasizes the word " _friends_ ".

Apparently, Elena notices that too, because she threads her fingers through his and looks at Stefan. "Stefan, I meant what I said. I want to be here … with Damon. I … I want him." The last word comes out as a barely-audible whisper, but it's enough to catch Stefan's notice.

"What?" He looks like his heart has been shattered into a million pieces. "Elena, I love you. How can you choose him? He's …"

"A lot more than you give him credit for," she finishes for him. "He's not the arrogant asshole you told me about. He's treated me with nothing but compassion since I've met him, Stefan. I'm sorry for doing this to you, but I'm _not_ sorry that I fell for him."

Her words make Damon snap his head up to look at her, his heart beating faster than ever as he asks her, "What did you just say?"

Her eyes soften as she brings their joined hands to her mouth, brushing her lips across his knuckles. "I love _you_ , Damon. You … only you."

Damon blinks his eyes, feeling a sudden unfamiliar burning in there as tears prickle them. "But-but I'm not perfect. He's the perfect one. Stefan was the perfect child to our parents. He was the perfect student when we were in school. I'm sure he's been nothing but the perfect boyfriend to you too," he rambles on, trying to make sense of what's happening.

Elena sniffles, wiping away at the tear tracks on her cheeks. "You're right. He's the perfect one," she says, and for a moment, Damon feels like his world is crushing down on him. He has lost the love of his parents for not being the perfect son. That loss has left him bitter and cold, but now, if he lost the affection of this woman over his brother, he knows he'll be broken for life.

As if she can hear his thoughts, Elena steps closer to him, putting a hand on his face. "Hey, let me finish. Yes, you're not perfect. But I don't care that you're not perfect like Stefan is, because your imperfections make it very hard to not to love you. You're perfect for me."

Stefan looks from Elena to his brother and back and then sighs, letting the first drop of tear escape his eyes. "So I lose the real game, huh?" he asks no one in particular.

His pain makes Damon realize that maybe … just maybe … his brother wasn't responsible for their parents' preferential behaviors all those years ago. In that moment, he feels his heart break for his brother's sadness. However, he can't make himself feel sorry for falling for Elena.

"Stef," he calls softly. "I'm really sorry. I'm sorry for always being a pain in your ass. I'm …" he stops talking when his brother holds a hand up to silence him.

"I need to be alone right now," he tells them both. "Goodbye."

With guilt and sadness crushing him, Damon watches his brother walk away from him, wondering if their relationship will be able to be repaired ever again.

Elena leans into his side and says, "Let him go. He needs to clear his head."

Her voice brings him back to where he stands with her in his arms. He sighs. "I never thought that stupid fucking bet will make things this worse."

Her eyes fly to meet his as she asks, "What bet?"

 _Fuck!_

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Sitting on his couch, Damon lets his eyes follow Elena's movements as she paces around the room. Finally, she stops in front of him and asks, "So let me get this straight. You're feeling guilty because you made a bet with Matt that you'll be able to make Elena Gilbert fall for you without falling in return, right?"

"More like feeling like a complete and utter fucktard and a douchebag, but …" he stops when he catches her eyes and clears his throat. "Right," he answers.

"Then you lost. So there's no need to feel guilty about that … or for stealing me from your brother. I was never his to begin with."

Her casual attitude confuses him. "What do you mean, Elena? You …"

"Katherine," she says abruptly.

"What …?"

"My name," she explains with a shrug. "It's Katherine Pierce, not Elena Gilbert. I'm her twin sister."

He feels a frown tugging on his eyebrows. "But you're dead. You told me so yourself."

"No," she responds with a shake of her head. "I'm alive. Elena is the one who got diagnosed with cancer. She was already dating Stefan when she found out and contacted me. There wasn't much I could do to help her so I agreed to do the one thing she asked of me."

She looks nervous as she peeks at his face before continuing. "I agreed to pretend to be Elena and then slowly distance myself from Stefan. So when I break up with him as Elena, it doesn't come as a shock to him, but rather two people falling out of love and getting distant."

"So you tricked him into thinking that you're Elena? Just so you can let him down easily?"

She lets out a dry humorless chuckle. "I guess that plan was blown out of the water, wasn't it?"

Damon nods slowly as the enormity of her disclosure dawns on him. "So I don't need to feel guilty for stealing my brother's girl, do I?"

She shakes her head. "No, you don't. We'll tell him when he's ready to listen." Silence hangs between them for a moment. Then she sighs and says, "I'm sorry you didn't get to win your bet though."

"It was a stupid bet," he says as he stands up. "I won big time though. I won something far more precious."

"What?"

He reaches out to pull her to his chest. "You. I love you, Katherine Pierce. I might have thought you were someone else, but it's _your_ heart I want … _you_ are who I love."

She closes the gap between them and brushes her lips against his. "Always."

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 **~*~*~*The End*~*~*~**

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 **A/N: So…thoughts?**

 **I'd love to hear what you think of this. So please, leave a review. :)**

 **Thanks for reading.**

 **Take care.**

 **Ann**


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